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Jack's Playground 28
Digital Playground (SKU: 102910)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Teen America: Mission 9
Digital Playground (SKU: 100666)
No Listings Currently Available
Jack`s at it again. This time, it`s even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack`s answer to getting a f*ckin` job!
Jack's Playground 26
Digital Playground (SKU: 100464)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 8
Digital Playground (SKU: 63638)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 29
Digital Playground (SKU: 103983)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 2
Digital Playground (SKU: 57957)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground, 6
Digital Playground (SKU: 61436)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 23
Digital Playground (SKU: 92271)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground
Digital Playground (SKU: 57295)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Teen America: Mission 11
Digital Playground (SKU: 103731)
No Listings Currently Available
Jack`s at it again. This time, it`s even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack`s answer to getting a f*ckin` job!
Jack's Playground 4
Digital Playground (SKU: 59660)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 7
Digital Playground (SKU: 62629)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 25
Digital Playground (SKU: 96160)
No Listings Currently Available
Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they’d do anything, he immed...
Jack's Teen America: Mission 17
Digital Playground (SKU: 123192)
No Listings Currently Available
Shot in High Definition. With six lovely ladies competing for the same title, it`s a tight race to the finish and Digital Playground contract stars, Jana Cova and Lacie Heart, are off to a succulent start. Lacie calls Scott her bitch before she takes his huge c*ck in her wet mouth and tight little p...
Jacks Teen America 23
Digital Playground (SKU: 196710)
No Listings Currently Available
This latest release from Digital Playground features Riley Steele and Stoya in intimate and seductive hardcore action! The Jacks Teen America series parodies beauty pageants and Jacks lovely contestants all compete for the crown. They take off their clothes, they masturbate, they suck, they fuck and...
Jack's Playground 34
Digital Playground (SKU: 131760)
No Listings Currently Available
Shot in High Definition. This new release stars Katsumi in her panty hose with More Anal and Lots of Fun Jack TV and Fine Ass Chicks, Titty-F*cking, C*ck-Sucking and Banging Their Way Into Music Video Stardom! This title is HOT HOT HOT!!!
Jack's Teen America: Mission 14
Digital Playground (SKU: 109692)
No Listings Currently Available
With five lovely ladies competing for the same title, which girl will take the honors? Will Brooke or Jamie get to deliver their acceptance speech? Did Jack vote for one of their amazingly anal delights? Does Sara stand a chance of winning with her delectable titty-f*ck offering? Is the slippery, we...
Jack's Teen America: Mission 15
Digital Playground (SKU: 114266)
No Listings Currently Available
Shot in HD. With five lovely ladies competing for the same title, it`s a tight race to the finish and Bree is off to a succulent start. She charms the judges and Scott Nails with her amazing body and gorgeous face. Alicia shows she`s got the stamina to go the distance as she works the treadmill, the...
Jack's My First Porn
Digital Playground (SKU: 103152)
No Listings Currently Available
MY FIRST PORN is a new line by acclaimed director Robby D. Shot entirely on HD, it spins off the multi-awarded Jack`s Playground and Jack`s Teen America series, showing everyone the comedic sex-spectacle of true, behind-the-scenes porn direction. Offering more anal than any other Digital Playground...
Jack's Playground 3
Digital Playground (SKU: 59293)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 17
Digital Playground (SKU: 83011)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 20
Digital Playground (SKU: 87103)
No Listings Currently Available
See real girls uncensored. Winner of AVN`s Venus Awards, Nightmoves for Best Gonzo Series. Playful, powerful, and supremely sexual - a revolutionary sex comedy... One of the most original series in years! -- AVN magazine
Jack's Playground 21
Digital Playground (SKU: 88895)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 22
Digital Playground (SKU: 89499)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 15
Digital Playground (SKU: 78524)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 11
Digital Playground (SKU: 73102)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 5
Digital Playground (SKU: 60987)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 31
Digital Playground (SKU: 110825)
No Listings Currently Available
Jack`s Playground 31, the superstar edition, stars the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP`s original contract star, Rocki Roads in brand new, never-before-seen footage. She lets Vince Vouyer spin her around and pleasure her all over. Jasmine Byrne does...
Jack's Playground 35
Digital Playground (SKU: 140161)
No Listings Currently Available
Jack is really busy casting for music videos and now he`s landed Digital Playground`s super fine contract star, Teagan Presley. She takes a big c*ck in the butt and we KNOW Scott Nails found some SWEET ASS pleasure deep in her crack. True to Jack`s good sense, there`s a lot of tease and a lot of act...
Jack's Playground: Big Ass Show
Digital Playground (SKU: 103727)
No Listings Currently Available
Jack`s at it again! But this time, he`s focusing in on hot babes with BIG, FUN ASSES. It`s more cushion for the pushin`. Forget professional... This volume is all about ASS. It`s hot and kinky and Jack`s found a new niche.
Jack's Playground 30
Digital Playground (SKU: 107406)
No Listings Currently Available
Directed by Robby D., JACK`S PLAYGROUND #30 is an incredibly insatiable, sexy installment of the multi-award winning Jack`s Playground line. This Robby D. series has been named Best Gonzo Series (AVN), Best All-Sex Series (Nightmoves), and Best Comedy Series (AFWG), and that`s just a few of the acco...
Jack's POV 3
Digital Playground (SKU: 114267)
No Listings Currently Available
You don`t know Jack until you`ve seen through his eyes. These bitches got skills! C*ck hungry hot babes! Satisfy all the ho`s!
Jack's Big Tit Show 4
Digital Playground (SKU: 136367)
No Listings Currently Available
Shot in High Definition. Jack is really busy casting for music videos and now he`s on the hunt for big, beautiful boobies. They bounce, and they shake. There`s more than a mouthful, more than a handful... Plenty of big boobies bursting out of their bras. Forget professional... This volume is all abo...
Jack's Teen America: Mission 13
Digital Playground (SKU: 106835)
No Listings Currently Available
Five horny teens. Two sound guys with equipment. One contest. One winner. Sound familiar? It is. It`s JACK`S TEEN AMERICA. Put it in and cast your vote! Jack`s at it again! But this time, it`s professional... and even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack`...
Jack's Teen America: Mission 10
Digital Playground (SKU: 102691)
No Listings Currently Available
Jack`s at it again. This time, it`s even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack`s answer to getting a f*ckin` job!
Jack's Big Tit Show 8
Digital Playground (SKU: 187778)
No Listings Currently Available
Jack is really busy casting for music videos and now he`s on the hunt for big, beautiful boobies. They bounce and they shake. There`s more than a mouthful, more than a handful... Plenty of massive melons bursting out of their bras. JACK`S BIG TIT SHOW 8 is all about the tantalizing titties of Gina L...
Jack's Playground 32
Digital Playground (SKU: 115434)
No Listings Currently Available
JACK`S PLAYGROUND #32 features Digital Playground`s contract babe, Sophia Santi, eager to make it in the music video scene. She shows her distinct talents and raw, exquisite beauty in two delectable scenes. Then Michelle Maylene proves she will do anything for fame too. Flower Tucci goes with the we...
Jack's Teen America: Mission 3
Digital Playground (SKU: 84653)
No Listings Currently Available
Jack`s at it again. This time, it`s even kinkier than before. Jack turns what he knows best into a career. Welcome to Jack`s answer to getting a f*ckin` job!
Jack's Playground 16
Digital Playground (SKU: 81282)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 18
Digital Playground (SKU: 84365)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 14
Digital Playground (SKU: 77725)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 12
Digital Playground (SKU: 75073)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 19
Digital Playground (SKU: 85602)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Playground 24
Digital Playground (SKU: 93876)
No Listings Currently Available
JACK`S PLAYGROUND is a collection of Jack`s personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they`d do anything, he immedia...
Jack's Big Ass Show 4
Digital Playground (SKU: 118944)
No Listings Currently Available
Shot in High Definition. In volume 4 of this ASS-A-LISCIOUS show, Jack shows some good old-fashioned nepotism as he enlists the hard-bodied Naomi to devirginize his cousin for an 18th birthday surprise. Naomi does the job, turns up the heat, and gives the young lads` future lovers stiff competition!...
Jack's Big Tit Show 5
Digital Playground (SKU: 140917)
No Listings Currently Available
Shot in High Definition. Jack is really busy casting for music videos and now he`s on the hunt for big, beautiful boobies. They bounce and they shake. There`s more than a mouthful, more than a handful plenty of big boobies bursting out of their bras. Forget professional... this volume is all about...
Meet The Twins 2
Northstar Associates (SKU: 113273)
No Listings Currently Available
If you love blondes with massive tits then grab this one while you can!!! We sold out of the first volume and this volume brings double the pleasure, double the fun, and double the D`s even double the F`s. These insatiable sluts love to have their titties f*cked!! Step on up and rub your c*ck betw...
Mother Fuckers 4
Mayhem (SKU: 133850)
No Listings Currently Available
Five hot and horny housewives go f*cking and sucking their way up and down the block while their husbands are slaving away at the office! You`ve got a front row seat for all the action as these nasty little homemakers get drilled hard and deep until their p*ssies are pounded raw. Watch their assh*...
Meet the Twins 11
Overboard Video (SKU: 151564)
No Listings Currently Available
These tits are so big you don`t need a trampoline to watch these babies bounce! You are at the home of some of the ripest melons you have ever set your eyes on! It is a tit worshipper`s feast - Tweak the nipples and smack the boobs and just watch them bounce around for your pleasure! We like to watc...